diff --git a/components/brave_vpn/brave_vpn_os_connection_api_win.cc b/components/brave_vpn/brave_vpn_os_connection_api_win.cc
index d587858c98b5..7a3c969466c8 100644
--- a/components/brave_vpn/brave_vpn_os_connection_api_win.cc
+++ b/components/brave_vpn/brave_vpn_os_connection_api_win.cc
@@ -17,7 +17,9 @@
 // (brian@clifton.me)'s work (https://github.com/bsclifton/winvpntool).
 
 using brave_vpn::internal::CheckConnectionResult;
+using brave_vpn::internal::CloseEventHandleForConnecting;
 using brave_vpn::internal::CreateEntry;
+using brave_vpn::internal::GetEventHandleForConnecting;
 using brave_vpn::internal::GetPhonebookPath;
 using brave_vpn::internal::PrintRasError;
 using brave_vpn::internal::RemoveEntry;
@@ -47,7 +49,9 @@ BraveVPNOSConnectionAPIWin::BraveVPNOSConnectionAPIWin() {
 }
 
 BraveVPNOSConnectionAPIWin::~BraveVPNOSConnectionAPIWin() {
-  CloseHandle(event_handle_);
+  CloseHandle(event_handle_for_connected_);
+  CloseHandle(event_handle_for_disconnected_);
+  CloseEventHandleForConnecting();
 }
 
 void BraveVPNOSConnectionAPIWin::CreateVPNConnection(
@@ -75,6 +79,10 @@ void BraveVPNOSConnectionAPIWin::Connect(const std::string& name) {
 }
 
 void BraveVPNOSConnectionAPIWin::Disconnect(const std::string& name) {
+  // Fire pseudo disconnecting noti because windows doesn't have it.
+  for (Observer& obs : observers_)
+    obs.OnIsDisconnecting(name);
+
   // Connection state update from this call will be done by monitoring.
   base::ThreadPool::PostTask(
       FROM_HERE, {base::MayBlock()},
@@ -100,7 +108,18 @@ void BraveVPNOSConnectionAPIWin::CheckConnection(const std::string& name) {
 void BraveVPNOSConnectionAPIWin::OnObjectSignaled(HANDLE object) {
   DCHECK(!target_vpn_entry_name().empty());
 
-  CheckConnection(target_vpn_entry_name());
+  CheckConnectionResult result = CheckConnectionResult::UNKNOWN;
+  if (object == GetEventHandleForConnecting()) {
+    result = CheckConnectionResult::CONNECTING;
+  } else if (object == event_handle_for_connected_) {
+    result = CheckConnectionResult::CONNECTED;
+  } else if (object == event_handle_for_disconnected_) {
+    result = CheckConnectionResult::DISCONNECTED;
+  } else {
+    NOTREACHED();
+  }
+
+  OnCheckConnection(target_vpn_entry_name(), result);
 }
 
 void BraveVPNOSConnectionAPIWin::OnCheckConnection(
@@ -109,9 +128,20 @@ void BraveVPNOSConnectionAPIWin::OnCheckConnection(
   if (result == CheckConnectionResult::UNKNOWN)
     return;
 
-  const bool connected = result == CheckConnectionResult::CONNECTED;
   for (Observer& obs : observers_) {
-    connected ? obs.OnConnected(name) : obs.OnDisconnected(name);
+    switch (result) {
+      case CheckConnectionResult::CONNECTED:
+        obs.OnConnected(name);
+        break;
+      case CheckConnectionResult::CONNECTING:
+        obs.OnIsConnecting(name);
+        break;
+      case CheckConnectionResult::DISCONNECTED:
+        obs.OnDisconnected(name);
+        break;
+      default:
+        break;
+    }
   }
 }
 
@@ -134,13 +164,24 @@ void BraveVPNOSConnectionAPIWin::OnRemoved(const std::string& name,
 }
 
 void BraveVPNOSConnectionAPIWin::StartVPNConnectionChangeMonitoring() {
-  DCHECK(!event_handle_);
-  event_handle_ = CreateEvent(nullptr, false, false, nullptr);
+  DCHECK(!event_handle_for_connected_ && !event_handle_for_disconnected_);
+
+  event_handle_for_connected_ = CreateEvent(nullptr, false, false, nullptr);
+  event_handle_for_disconnected_ = CreateEvent(nullptr, false, false, nullptr);
 
+  // We don't need to check current connection state again if monitor each event
+  // separately.
+  RasConnectionNotificationW(static_cast<HRASCONN>(INVALID_HANDLE_VALUE),
+                             event_handle_for_connected_, RASCN_Connection);
   RasConnectionNotificationW(static_cast<HRASCONN>(INVALID_HANDLE_VALUE),
-                             event_handle_,
-                             (RASCN_Connection | RASCN_Disconnection));
-  watcher_.StartWatchingMultipleTimes(event_handle_, this);
+                             event_handle_for_disconnected_,
+                             RASCN_Disconnection);
+  connected_event_watcher_.StartWatchingMultipleTimes(
+      event_handle_for_connected_, this);
+  disconnected_event_watcher_.StartWatchingMultipleTimes(
+      event_handle_for_disconnected_, this);
+  connecting_event_watcher_.StartWatchingMultipleTimes(
+      GetEventHandleForConnecting(), this);
 }
 
 }  // namespace brave_vpn
diff --git a/components/brave_vpn/brave_vpn_os_connection_api_win.h b/components/brave_vpn/brave_vpn_os_connection_api_win.h
index a72dae851506..5dcc615603a3 100644
--- a/components/brave_vpn/brave_vpn_os_connection_api_win.h
+++ b/components/brave_vpn/brave_vpn_os_connection_api_win.h
@@ -51,8 +51,11 @@ class BraveVPNOSConnectionAPIWin : public BraveVPNOSConnectionAPI,
 
   void StartVPNConnectionChangeMonitoring();
 
-  HANDLE event_handle_ = nullptr;
-  base::win::ObjectWatcher watcher_;
+  HANDLE event_handle_for_connected_ = nullptr;
+  HANDLE event_handle_for_disconnected_ = nullptr;
+  base::win::ObjectWatcher connected_event_watcher_;
+  base::win::ObjectWatcher connecting_event_watcher_;
+  base::win::ObjectWatcher disconnected_event_watcher_;
   base::WeakPtrFactory<BraveVPNOSConnectionAPIWin> weak_factory_{this};
 };
 
diff --git a/components/brave_vpn/utils_win.cc b/components/brave_vpn/utils_win.cc
index 29cc018fbbfa..f1a77aa6b296 100644
--- a/components/brave_vpn/utils_win.cc
+++ b/components/brave_vpn/utils_win.cc
@@ -18,6 +18,25 @@ namespace brave_vpn {
 
 namespace {
 
+HANDLE g_event_handle = nullptr;
+
+void WINAPI RasDialFunc(UINT, RASCONNSTATE rasconnstate, DWORD error) {
+  if (error) {
+    internal::PrintRasError(error);
+    return;
+  }
+
+  // Only interested in connecting event.
+  switch (rasconnstate) {
+    case RASCS_ConnectDevice:
+      SetEvent(g_event_handle);
+      break;
+    default:
+      // Ignore all other states.
+      break;
+  }
+}
+
 // https://docs.microsoft.com/en-us/windows/win32/api/winbase/nf-winbase-formatmessage
 void PrintSystemError(DWORD error) {
   constexpr DWORD kBufSize = 512;
@@ -57,6 +76,19 @@ DWORD SetCredentials(LPCTSTR entry_name, LPCTSTR username, LPCTSTR password) {
 
 namespace internal {
 
+HANDLE GetEventHandleForConnecting() {
+  if (!g_event_handle)
+    g_event_handle = CreateEvent(nullptr, false, false, nullptr);
+  return g_event_handle;
+}
+
+void CloseEventHandleForConnecting() {
+  if (g_event_handle) {
+    CloseHandle(g_event_handle);
+    g_event_handle = nullptr;
+  }
+}
+
 // https://docs.microsoft.com/en-us/windows/win32/api/ras/nf-ras-rasgeterrorstringa
 void PrintRasError(DWORD error) {
   constexpr DWORD kBufSize = 512;
@@ -197,8 +229,8 @@ bool ConnectEntry(const std::wstring& entry_name) {
 
   DVLOG(2) << "Connecting to " << entry_name;
   HRASCONN h_ras_conn = NULL;
-  dw_ret = RasDial(NULL, DEFAULT_PHONE_BOOK, lp_ras_dial_params, NULL, NULL,
-                   &h_ras_conn);
+  dw_ret = RasDial(NULL, DEFAULT_PHONE_BOOK, lp_ras_dial_params, 0,
+                   (LPVOID)(&RasDialFunc), &h_ras_conn);
   if (dw_ret != ERROR_SUCCESS) {
     HeapFree(GetProcessHeap(), 0, (LPVOID)lp_ras_dial_params);
     PrintRasError(dw_ret);
@@ -324,6 +356,37 @@ bool CreateEntry(const std::wstring& entry_name,
   return true;
 }
 
+CheckConnectionResult GetConnectionState(HRASCONN h_ras_conn) {
+  DWORD dw_ret = 0;
+
+  RASCONNSTATUS ras_conn_status;
+  ZeroMemory(&ras_conn_status, sizeof(RASCONNSTATUS));
+  ras_conn_status.dwSize = sizeof(RASCONNSTATUS);
+
+  // Checking connection status using RasGetConnectStatus
+  dw_ret = RasGetConnectStatus(h_ras_conn, &ras_conn_status);
+  if (ERROR_SUCCESS != dw_ret) {
+    LOG(ERROR) << "RasGetConnectStatus failed: Error = " << dw_ret;
+    return CheckConnectionResult::UNKNOWN;
+  }
+
+  switch (ras_conn_status.rasconnstate) {
+    case RASCS_ConnectDevice:
+      VLOG(2) << "Connecting device...";
+      return CheckConnectionResult::CONNECTING;
+    case RASCS_Connected:
+      VLOG(2) << "Connection completed";
+      return CheckConnectionResult::CONNECTED;
+    case RASCS_Disconnected:
+      VLOG(2) << "Disconnected";
+      return CheckConnectionResult::DISCONNECTED;
+    default:
+      break;
+  }
+
+  return CheckConnectionResult::DISCONNECTED;
+}
+
 CheckConnectionResult CheckConnection(const std::wstring& entry_name) {
   if (entry_name.empty())
     return CheckConnectionResult::UNKNOWN;
@@ -339,7 +402,7 @@ CheckConnectionResult CheckConnection(const std::wstring& entry_name) {
 
   // If got success here, it means there is no connected vpn entry.
   if (dw_ret == ERROR_SUCCESS) {
-    return CheckConnectionResult::NOT_CONNECTED;
+    return CheckConnectionResult::DISCONNECTED;
   }
 
   // Abnormal situation.
@@ -367,10 +430,10 @@ CheckConnectionResult CheckConnection(const std::wstring& entry_name) {
   }
 
   // If successful, find connection with |entry_name|.
-  CheckConnectionResult result = CheckConnectionResult::NOT_CONNECTED;
+  CheckConnectionResult result = CheckConnectionResult::DISCONNECTED;
   for (DWORD i = 0; i < dw_connections; i++) {
     if (entry_name.compare(lp_ras_conn[i].szEntryName) == 0) {
-      result = CheckConnectionResult::CONNECTED;
+      result = GetConnectionState(lp_ras_conn[i].hrasconn);
       break;
     }
   }
diff --git a/components/brave_vpn/utils_win.h b/components/brave_vpn/utils_win.h
index 8559e15ea818..e8bfb98f5f4f 100644
--- a/components/brave_vpn/utils_win.h
+++ b/components/brave_vpn/utils_win.h
@@ -15,7 +15,8 @@ namespace internal {
 
 enum class CheckConnectionResult {
   CONNECTED,
-  NOT_CONNECTED,
+  CONNECTING,
+  DISCONNECTED,
   UNKNOWN,
 };
 
@@ -29,6 +30,9 @@ bool CreateEntry(const std::wstring& entry_name,
 bool RemoveEntry(const std::wstring& entry_name);
 bool DisconnectEntry(const std::wstring& entry_name);
 bool ConnectEntry(const std::wstring& entry_name);
+// Don't cache returned HANDLE. It could be invalidated.
+HANDLE GetEventHandleForConnecting();
+void CloseEventHandleForConnecting();
 
 CheckConnectionResult CheckConnection(const std::wstring& entry_name);